Details of the Drug

General Information of Drug (ID: DMXYTN9)

Drug Name

Phenmetrazine

Synonyms

Cafilon; Defenmetrazin; Dexphenmetrazine; Fenmetrazin; Fenmetrazina; Oxazimedrine; Phenmetraline; Phenmetrazin; Phenmetrazinum; Preludin hydrochloride; A 66; Psychamine A 66; Defenmetrazin (TN); Fenmetrazin (TN); Fenmetrazina [INN-Spanish]; Oxazimedrine (TN); Phenmetraline (TN); Phenmetrazine [INN:BAN]; Phenmetrazinum [INN-Latin]; Dl-2-Phenyl-3-methyltetrahydro-1,4-oxazine; 2-Fenyl-3-methylmorfolin; 2-Fenyl-3-methylmorfolin [Czech]; 2-Phenyl-3-methylmorpholine; 3-Methyl-2-phenylmorpholine; 3-Methyl-2-phenyltetrahydro-2H-1,4-oxazine

Indication

Disease Entry	ICD 11	Status	REF
Obesity	5B81	Approved	[1]

Therapeutic Class

Appetite Depressants

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

177.24

Topological Polar Surface Area (xlogp)

1.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Elimination: 19% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 16 - 31 hours [3]
Metabolism: The drug is metabolized via the hepatic [4]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 6.0447 micromolar/kg/day [5]
Water Solubility: The ability of drug to dissolve in water is measured as 2.5 mg/mL [2]

Chemical Identifiers

Formula: C11H15NO
IUPAC Name: 3-methyl-2-phenylmorpholine
Canonical SMILES: CC1C(OCCN1)C2=CC=CC=C2
InChI: InChI=1S/C11H15NO/c1-9-11(13-8-7-12-9)10-5-3-2-4-6-10/h2-6,9,11-12H,7-8H2,1H3
InChIKey: OOBHFESNSZDWIU-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 4762
ChEBI ID: CHEBI:8067
CAS Number: 134-49-6
DrugBank ID: DB00830
TTD ID: D0M2MC
VARIDT ID: DR01097

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Dopamine transporter (DAT)	TTVBI8W	SC6A3_HUMAN	Inhibitor	[6]
Norepinephrine transporter (NET)	TTAWNKZ	SC6A2_HUMAN	Inhibitor	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Obesity

ICD Disease Classification

5B81

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Dopamine transporter (DAT)	DTT	SLC6A3	1.08E-03	-3.08	-1.99

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Drug information of Phenmetrazine, 2008. eduDrugs.
2	BDDCS applied to over 900 drugs
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
5	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6	Interaction of the anorectic medication, phendimetrazine, and its metabolites with monoamine transporters in rat brain. Eur J Pharmacol. 2002 Jun 28;447(1):51-7.
7	Augmentation effect of combination therapy of aripiprazole and antidepressants on forced swimming test in mice. Psychopharmacology (Berl). 2009 Sep;206(1):97-107.
8	Treatment of comorbid pain with serotonin norepinephrine reuptake inhibitors. CNS Spectr. 2008 Jul;13(7 Suppl 11):22-6.
9	Invivo antioxidant status: a putative target of antidepressant action. Prog Neuropsychopharmacol Biol Psychiatry. 2009 Mar 17;33(2):220-8.
10	Differential involvement of the norepinephrine, serotonin and dopamine reuptake transporter proteins in cocaine-induced taste aversion. Pharmacol Biochem Behav. 2009 Jul;93(1):75-81.
11	Clinically relevant drug interactions with new generation antidepressants and antipsychotics. Ther Umsch. 2009 Jun;66(6):485-92.
12	2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
13	Antidepressants suppress production of the Th1 cytokine interferon-gamma, independent of monoamine transporter blockade. Eur Neuropsychopharmacol. 2006 Oct;16(7):481-90.
14	Multi-target therapeutics: when the whole is greater than the sum of the parts. Drug Discov Today. 2007 Jan;12(1-2):34-42.
15	Dasotraline for the Treatment of Attention-Deficit/Hyperactivity Disorder: A Randomized, Double-Blind, Placebo-Controlled, Proof-of-Concept Trial in Adults. Neuropsychopharmacology. 2015 Nov;40(12):2745-52.
16	Imaging the effects of methylphenidate on brain dopamine: new model on its therapeutic actions for attention-deficit/hyperactivity disorder. Biol Psychiatry. 2005 Jun 1;57(11):1410-5.
17	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
18	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
19	Synthesis and pharmacology of site-specific cocaine abuse treatment agents: restricted rotation analogues of methylphenidate. J Med Chem. 2007 May 31;50(11):2718-31.
20	Rapid detection of Parkinson's disease by SPECT with altropane: a selective ligand for dopamine transporters. Synapse. 1998 Jun;29(2):128-41.
21	Anti-obesity drugs. Expert Opin Pharmacother. 2008 Jun;9(8):1339-50.
22	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 927).